I'm looking for the squishiest leather hobo I can afford.

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Are you in Europe? Both Liebeskind and Fredsbruder brands have lovely soft, squishy leather and an affordable price point. If you want delicious vintage-y leather, look at Campomaggi - a little more expensive, but really lush leather and maybe quite akin to your Scaramanga bag in style. The squishiest hobo I've ever owned was an Hugo Boss lambskin - it was huge and totally flaccid though (...ahem...) and I could never find anything in it, so I offed it. Ah, nostalgia...

- Lips <now humming theme tune to 'littlest hobo'>
Yes. The Liebeskind. Also Linea Pelle. Really nice smooshy leathers. :-)
 
The Furla Elisabeth could be an option. I have one in black pebbled leather and it's a squooshy black puddle of a bag.

Good luck in your quest and let us know what you end up getting!
 
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